This is a corny title. It is also an idiom that seems quite obvious — who wants to think of themselves as closed minded, or someone that always does the same thing every time?

When I was a kid, I was convinced Google was going to be huge before it IPO’d, and begged my dad to invest some money in it. When he didn’t, every year afterward when I had a chance as a kid I’d bring it up smugly. “Look who was right,” I’d tell him, and think to myself how open minded and smart I was (as any teen was known to do). If we had invested even a little bit, we’d be rich!

But as I’ve grown older, I’ve noticed I’ve gathered a heavy layer of skepticism regarding new technologies, new startups, and just programming in general. If a new startup or piece of technology comes out that I either A) Know there are very, very hard problems to solve or B) know the market is either really crowded or extremely niche, I’ve tended to dismiss them. This wasn’t made as clear to me as when I was reading over the Hacker News thread “April 5, 2007: “Show HN, Dropbox”. It was a glimpse into a thread from the past talking about Dropbox when it was announced. What surprised me most were the comments — very few people were encouraging, and in fact, many where skeptical. The more I read back on those comments, however, the more I realized I agreed with what a lot of the people were saying — I would have probably wondered how Dropbox was better than a thumb drive, or how it differed from XYZ tool already out there. And yet, roughly 6 years later, Dropbox is a billion dollar company.

I’ve never wanted to be the “…No wireless. Less space than a nomad. Lame.” person. We all look back and see how foolish that statement was. But the other day, as I thought about bitcoin, a technology I was excited about, I looked into my chat history and found that, in 2011, I had been given a chance to mine bitcoins when they were ~$2 per coin. A friend begged me to join her mining pool, and she seemed really excited. I, of course, was skeptical, and while I didn’t dismiss the idea, I didn’t get back to her. That definitely bummed me out.

Here’s the thing — I know hindsight is 20/20. You can always look back and think about the things you could have done, and how it would have changed your life (or improved it) in many ways. You can’t change those decisions, and with some there was probably a good deal of risk that 99% of the time, would not have paid off. I know or have read about many a programmer who could have been employee #1 at BigStartupCo, and they kick themselves every day about it. Don’t be that person — not many people can take the huge risks involved (lower salary, moving, long long hours) and even then, they may not pay off. But what would it have really hurt to buy $30 worth of bitcoins back in 2009? Or mined them for a month, or just a few days? The only thing it would have taken was A) A bit of my time, and/or B) A bit of my money. And while time and money are important, I know I’ve spent time and money on things that were trivial and unimportant (watching TV shows, buying movies, etc), when I could have used it to take another risk.

There’s been other opportunities I’ve squandered as well, but with other people. Back when I hosted my first hackathon, I got a few emails from very excited people who wanted to talk after it was all done. To be frank I was more interested in talking to people who seemed busy, or were what I thought were amazing programmers, because those were the people I was excited about. Time passed and even when I wanted to email the people that had originally been very excited to talk to me, I felt like it would have been an insult to get back to them late in the game. I’ve seen quite a few of them since then, and it’s been amazing to see their development into rockstar developers, entrepreneurs, or just amazing people. It wouldn’t have hurt me to meet with them, and in fact it could have only helped me meet amazing people.

So, my new strategy is this: if someone, anyone, gets really excited about a technology, if it’s easy to get into or takes just a little bit of my time and money, I’ll do it. If there’s a startup that announces itself and it’s free to sign up and doesn’t look scummy, I’m going to sign up for it. Who cares if it’s been done 1000 times before, it hurts you 0% to sign up (well, unless you use a common password across everything, then it might hurt you). The one time I took this strategy in the past was with Copy — an app very similar to Dropbox. I saw it on Facebook posted by a friend, and signed up during beta — they ended up giving 100GB to beta users now and forever, and it is my largest cloud hard drive I have that is 100%, totally free.

Finally, if someone is excited to talk, or just gets excited in general about anything, I’m going to try to talk with them. With my batting record so far, I have no good guesses as to who will end up being the next great entrepreneur, or what will be the next big technology. But so far, I’ve been much more wrong than right. So why not try doing the opposite of what I first think, and see where it takes me? At the very least, it will feel good to try new things.